ORGANIC
LETTERS
2010
Vol. 12, No. 24
5612-5615
Tetraureas versus Triureas in Sulfate
Binding
Chuandong Jia,†,§ Biao Wu,*,†,‡ Shaoguang Li,†,§ Xiaojuan Huang,† and
Xiao-Juan Yang*,†
State Key Laboratory for Oxo Synthesis & SelectiVe Oxidation, Lanzhou Institute of
Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China, College of
Chemistry & Materials Science, Northwest UniVersity, Xi’an, 710069, China, and
Graduate UniVersity of Chinese Academy of Sciences, Beijing 100049, China
wubiao@lzb.ac.cn; yangxj@lzb.ac.cn
Received September 19, 2010
ABSTRACT
By mimicking the scaffolds of oligopyridine-based ligands, triurea and tetraurea receptors have been developed for sulfate binding. The
triureas (L1, L2) show stronger binding of sulfate than tetraureas (L3, L4) in DMSO because of their better conformational complementarity with
sulfate, while the tetraureas display better “water tolerance” benefiting from the chelate effect and hydrophobic effect.
The design of sulfate receptors is a focus in anion receptor
chemistry1 due to their promising applications in anion
templated synthesis,2 transmembrane anion transport,3 and
nuclear waste remediation.4 In recent years, various sulfate
receptors have been developed with the macrocyclic,2,5
helical,6 tripodal,7 or podant backbones,8 and metal ion-
assisted frameworks.9 As required in environmentally and
biologically related applications, selective binding of sulfate
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† Lanzhou Institute of Chemical Physics.
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‡ Northwest University.
§ Graduate University of Chinese Academy of Sciences.
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10.1021/ol102221x 2010 American Chemical Society
Published on Web 11/15/2010